Fluoroalkanesulfonamide derivatives are compounds useful as organic intermediates. They are compounds that are expected, for example, as monomers corresponding to the next generation photoresist.
It is known that fluoroalkanesulfonamide derivatives or their analogous compounds can be synthesized, for example, by each process of the following Process “a” to Process “d”.
[Process “a”]
It is an example (Non-patent Publication 1) in which trifluoromethanesulfonic anhydride(CF3SO2)2Ois reacted with 1-bicyclo[2,2,1]hept-5-en-2-ylmethaneamine in an anhydrous methylene chloride solvent in the presence of triethylamine as a base.[Process “b”]
It is an example (Non-patent Publication 2) in which trifluoromethanesulfonic fluorideCF3SO2Fis reacted with 1-bicyclo[2,2,1]hept-5-en-2-ylmethaneamine in an anhydrous methylene chloride solvent in the presence of triethylamine as a base.[Process “c”]
It is an example (Non-patent Publication 2) of synthesizing trifluoromethanesulfonic anilide by using trifluoromethanesulfonic chlorideCF3SO2Clas a sulfonation agent, and by reacting this with aniline in the presence of pyridine as a base, in an anhydrous ether solvent.[Process “d”]
It is an example (Non-patent Publication 1) of synthesizing N-(m-trifluoromethylphenylsulfonyl)-5-aminomethylbicyclo[2.2.1]hept-2-ene by using m-trifluoromethylphenylsulfonic chloride as a sulfonation agent, and by reacting this with 1-bicyclo[2,2,1]hept-5-en-2-ylmethaneamine in the presence of 20% sodium hydroxide solution as a base, in an ether solvent.
Besides, Patent Publications 1-3, etc. are known as reaction examples of forming a [—SO2—NH—] bond by reacting a sulfonic halide containing a trifluoromethyl group with an amine-series compound.
[Non-patent Publication 1] Zhurnal OrganicheskoiKhimii (Russia), (1995), 31 (3), p. 357-64
[Non-patent Publication 2] Journal of Chemical Society, vol. 6 (5), p. 2574-2578 (published in 1957)
[Patent Publication 1] Japanese Patent Application Publication 8-81436
[Patent Publication 2] Japanese Patent Application Publication 11-209338
[Patent Publication 3] International Publication 97/23448 Pamphlet